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MedKoo Cat#: 597570 | Name: Dansyllysine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Dansyllysine is used to study binding conformations of drugs to human serum albumin and is used as a template molecule to form molecularly imprinted monolayers (MIMs) useful to produce optical biosensor recognition elements.

Chemical Structure

Dansyllysine
Dansyllysine
CAS#1101-84-4

Theoretical Analysis

MedKoo Cat#: 597570

Name: Dansyllysine

CAS#: 1101-84-4

Chemical Formula: C18H25N3O4S

Exact Mass: 379.1566

Molecular Weight: 379.47

Elemental Analysis: C, 56.97; H, 6.64; N, 11.07; O, 16.86; S, 8.45

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Synonym
Dansyllysine; Dns-lysine; N(epsilon)-Dansyl-L-lysine;
IUPAC/Chemical Name
N6-((5-(dimethylamino)naphthalen-1-yl)sulfonyl)-L-lysine
InChi Key
VQPRNSWQIAHPMS-HNNXBMFYSA-N
InChi Code
InChI=1S/C18H25N3O4S/c1-21(2)16-10-5-8-14-13(16)7-6-11-17(14)26(24,25)20-12-4-3-9-15(19)18(22)23/h5-8,10-11,15,20H,3-4,9,12,19H2,1-2H3,(H,22,23)/t15-/m0/s1
SMILES Code
N[C@@H](CCCCNS(=O)(C1=C2C=CC=C(N(C)C)C2=CC=C1)=O)C(O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 379.47 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Schwyzer R, Schiller PW. [Hormone-receptor-relationships: synthesis and characteristics of N-epsilon-dansyllysine 21-adrenocorticotropin-(1-24)-tetrakosipeptide]. Helv Chim Acta. 1971;54(3):897-904. German. PubMed PMID: 4323959. 2: Schiller PW. Study of adrenocorticotropic hormone conformation by evaluation of intramolecular resonance energy transfer in N -dansyllysine 21 -ACTH-(1-24)-tetrakosipeptide. Proc Natl Acad Sci U S A. 1972 Apr;69(4):975-9. PubMed PMID: 4337249; PubMed Central PMCID: PMC426607. 3: Frehland E, Kreikenbohm R, Pohl WG. Steady-state fluorescence polarization in planar lipid membranes. Experimental and theoretical analysis of the fluorophores 8-anilino-1-naphthalenesulfonate, 1,6-Diphenyl-1,3,5-hexatriene, dansyllysine-valinomycin and n-(9-anthroyloxy) fatty acids. Biophys Chem. 1982 Apr;15(1):73-86. PubMed PMID: 17000423. 4: Pohl GW, Knoll W, Gisin BF, Stark G. Optical and electrical studies on dansyllysine-valinomycin in thin lipid membranes. Biophys Struct Mech. 1976 Aug 23;2(2):119-37. PubMed PMID: 963233. 5: Kersteen EA, Barrows SR, Raines RT. Catalysis of protein disulfide bond isomerization in a homogeneous substrate. Biochemistry. 2005 Sep 13;44(36):12168-78. PubMed PMID: 16142915; PubMed Central PMCID: PMC2526094. 6: Hayamizu T, Kudoh S, Nakamura H. Methylated Nepsilon-dansyl-L-lysine as a fluorogenic reagent for the chiral separation of carboxylic acids. J Chromatogr B Biomed Sci Appl. 1998 Jun 12;710(1-2):211-8. PubMed PMID: 9686889. 7: Berezowska I, Lemieux C, Chung NN, Zelent B, Schiller PW. Dansylated analogues of the opioid peptide [Dmt1]DALDA: in vitro activity profiles and fluorescence parameters. Acta Biochim Pol. 2004;51(1):107-13. PubMed PMID: 15094830. 8: Motafakkerazad R, Wang MY, Wada N, Matsugo S, Konishi T. Simple HPLC evaluation of lipoamidase activity in tissue using a newly synthesized fluorescent substrate, dansyl-α-lipoyllysine. J Nutr Sci Vitaminol (Tokyo). 2011;57(5):377-82. Erratum in: J Nutr Sci Vitaminol (Tokyo). 2012;58(1):68. PubMed PMID: 22293216. 9: Babin F, Huynh-Dinh T. Chemical and enzymatic oxidative coupling of 5-hydroxy-N,N-dimethyltryptamine with amines. J Med Chem. 1987 Jul;30(7):1239-41. PubMed PMID: 3599029. 10: Chen T, Wong KF, Fenske DB, Palmer LR, Cullis PR. Fluorescent-labeled poly(ethylene glycol) lipid conjugates with distal cationic headgroups. Bioconjug Chem. 2000 May-Jun;11(3):433-7. PubMed PMID: 10821661. 11: Takahashi H, Suzuki E, Shimada I, Arata Y. Dynamical structure of the antibody combining site as studied by 1H-15N shift correlation NMR spectroscopy. Biochemistry. 1992 Mar 10;31(9):2464-8. PubMed PMID: 1547231. 12: Watson AL, Palmer ME, Burton G. Human chorionic gonadotrophin release and tissue viability in placental organ culture. Hum Reprod. 1995 Aug;10(8):2159-64. PubMed PMID: 8567859. 13: Arata Y, Kato K, Takahashi H, Shimada I. Nuclear magnetic resonance study of antibodies: a multinuclear approach. Methods Enzymol. 1994;239:440-64. Review. PubMed PMID: 7830594. 14: Rice GC, Fisher KA, Fisher GA, Hahn GM. Correlation of mammalian cell killing by heat shock to intramembranous particle aggregation and lateral phase separation using fluorescence-activated cell sorting. Radiat Res. 1987 Nov;112(2):351-64. PubMed PMID: 3120236. 15: Anderson RL, Kapp DS, Woo SY, Rice GC, Lee KJ, Hahn GM. Predictive assays for tumor response to single and multiple fractions of hyperthermia. Recent Results Cancer Res. 1988;109:239-49. PubMed PMID: 2845533. 16: Davies CL, Kovacs M. Measurement of DNA and antigen expression of live cells using three fluorochromes and two detectors. Cytometry. 1990;11(4):533-8. PubMed PMID: 1693115. 17: Mesaros JM, Luo G, Roeraade J, Ewing AG. Continuous electrophoretic separations in narrow channels coupled to small-bore capillaries. Anal Chem. 1993 Nov 15;65(22):3313-9. PubMed PMID: 8291681. 18: Humphries GM, Lovejoy JP. Cholesterol-free phospholipid domains may be the membrane feature selected by N epsilon-dansyl-L-lysine and merocyanine 540. Biochem Biophys Res Commun. 1983 Mar 16;111(2):768-74. PubMed PMID: 6404276. 19: Anderson RL, Shiu E, Fisher GA, Hahn GM. DNA damage does not appear to be a trigger for thermotolerance in mammalian cells. Int J Radiat Biol. 1988 Aug;54(2):285-98. PubMed PMID: 2900284. 20: Kim H, Kato K, Yamato S, Igarashi T, Matsunaga C, Ohtsuka H, Higuchi A, Nomura N, Noguchi H, Arata Y. Application of 13C NMR spectroscopy to paratope mapping for larger antigen-Fab complexes. FEBS Lett. 1994 Jun 13;346(2-3):246-50. PubMed PMID: 8013642.